Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactams

3-Oxidopyraziniums are azomethine ylides derived from 2(1H)-pyrazinones that can undergo 1,3-dipolar cycloadditions with acrylate and acrylic acid derivatives. The cycloaddition of 1-(4-methoxybenzyl)-5,6-dimethyl-3-oxidopyrazinium with methyl and tert-butyl acrylate and with methyl crotonate afford...

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Detalles Bibliográficos
Autores: Riesco-Llach, Gerard, Planas i Grabuleda, Marta, Feliu Soley, Lidia, Joule, John A.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/24593
Acceso en línea:http://hdl.handle.net/10256/24593
Access Level:acceso abierto
Palabra clave:Reaccions d'addició
Addition reactions
Ciclització (Química)
Ring formation (Chemistry)
Compostos orgànics
Organic compounds
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spelling Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactamsRiesco-Llach, GerardPlanas i Grabuleda, MartaFeliu Soley, LidiaJoule, John A.Reaccions d'addicióAddition reactionsCiclització (Química)Ring formation (Chemistry)Compostos orgànicsOrganic compounds3-Oxidopyraziniums are azomethine ylides derived from 2(1H)-pyrazinones that can undergo 1,3-dipolar cycloadditions with acrylate and acrylic acid derivatives. The cycloaddition of 1-(4-methoxybenzyl)-5,6-dimethyl-3-oxidopyrazinium with methyl and tert-butyl acrylate and with methyl crotonate afforded a 3,8-diazabicyclo[3.2.1]octane in 51–73% yield together with traces of the 2,5-diazabicyclo[2.2.2]octane. In contrast, cycloaddition of this 3-oxidopyrazinium with methyl 2-phenyl acrylate provided the [2.2.2] product in 40% yield. Herein, we show that the 2,5-diazabicyclo[2.2.2]octanes were formed from the [3.2.1] compounds via a Wagner–Meerwein rearrangement. Remarkably, when acrylic acid and 2-phenylacrylic acid were employed as dipolarophiles, novel tricyclic fused lactone-lactam systems were obtained in 71% and 50% yields, respectively. The formation of these tricyclic compounds can be rationalized via the mechanism described above followed by lactonization of the 2,5-diazabicyclo[2.2.2]octaneOpen Access funding provided thanks to the CRUE-CSIC agreement with American Chemical Society (ACS)American Chemical Society (ACS)2024info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionpeer-reviewedapplication/pdfhttp://hdl.handle.net/10256/24593The Journal of Organic Chemistry (JOC), 2024, vol. 89, núm. 5, p. 2904-2915Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.3c02273info:eu-repo/semantics/altIdentifier/issn/0022-3263info:eu-repo/semantics/altIdentifier/eissn/1520-6904Attribution 4.0 Internationalhttp://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:recercat.cat:10256/245932026-05-29T05:05:01Z
dc.title.none.fl_str_mv Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactams
title Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactams
spellingShingle Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactams
Riesco-Llach, Gerard
Reaccions d'addició
Addition reactions
Ciclització (Química)
Ring formation (Chemistry)
Compostos orgànics
Organic compounds
title_short Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactams
title_full Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactams
title_fullStr Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactams
title_full_unstemmed Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactams
title_sort Exploiting 3‑oxidopyraziniums toward diazabicyclo [3.2.1] octanes and their conversion into diazabicyclo [2.2.2] octanes and tricyclic lactone-lactams
dc.creator.none.fl_str_mv Riesco-Llach, Gerard
Planas i Grabuleda, Marta
Feliu Soley, Lidia
Joule, John A.
author Riesco-Llach, Gerard
author_facet Riesco-Llach, Gerard
Planas i Grabuleda, Marta
Feliu Soley, Lidia
Joule, John A.
author_role author
author2 Planas i Grabuleda, Marta
Feliu Soley, Lidia
Joule, John A.
author2_role author
author
author
dc.subject.none.fl_str_mv Reaccions d'addició
Addition reactions
Ciclització (Química)
Ring formation (Chemistry)
Compostos orgànics
Organic compounds
topic Reaccions d'addició
Addition reactions
Ciclització (Química)
Ring formation (Chemistry)
Compostos orgànics
Organic compounds
description 3-Oxidopyraziniums are azomethine ylides derived from 2(1H)-pyrazinones that can undergo 1,3-dipolar cycloadditions with acrylate and acrylic acid derivatives. The cycloaddition of 1-(4-methoxybenzyl)-5,6-dimethyl-3-oxidopyrazinium with methyl and tert-butyl acrylate and with methyl crotonate afforded a 3,8-diazabicyclo[3.2.1]octane in 51–73% yield together with traces of the 2,5-diazabicyclo[2.2.2]octane. In contrast, cycloaddition of this 3-oxidopyrazinium with methyl 2-phenyl acrylate provided the [2.2.2] product in 40% yield. Herein, we show that the 2,5-diazabicyclo[2.2.2]octanes were formed from the [3.2.1] compounds via a Wagner–Meerwein rearrangement. Remarkably, when acrylic acid and 2-phenylacrylic acid were employed as dipolarophiles, novel tricyclic fused lactone-lactam systems were obtained in 71% and 50% yields, respectively. The formation of these tricyclic compounds can be rationalized via the mechanism described above followed by lactonization of the 2,5-diazabicyclo[2.2.2]octane
publishDate 2024
dc.date.none.fl_str_mv 2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
peer-reviewed
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/24593
url http://hdl.handle.net/10256/24593
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/acs.joc.3c02273
info:eu-repo/semantics/altIdentifier/issn/0022-3263
info:eu-repo/semantics/altIdentifier/eissn/1520-6904
dc.rights.none.fl_str_mv Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution 4.0 International
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society (ACS)
publisher.none.fl_str_mv American Chemical Society (ACS)
dc.source.none.fl_str_mv The Journal of Organic Chemistry (JOC), 2024, vol. 89, núm. 5, p. 2904-2915
Articles publicats (D-Q)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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